Chlorosulfonyl isocyanate

Structural formula
General
Surname	Chlorosulfonyl isocyanate
other names	N -carbonylsulfamoyl chloride N -carbonylsulfamic acid chloride Sulfuryl chloride isocyanate Isocyanatosulfonyl chloride CSI
Molecular formula	ClSO 2 NCO
Brief description	colorless liquid with a pungent odor
External identifiers / databases
CAS number 1189-71-5 EC number 214-715-2 ECHA InfoCard 100.013.378 PubChem 70918 Wikidata Q8214963
properties
Molar mass	141.53 g mol −1
Physical state	liquid
density	1.63 g cm −3
Melting point	−44 ° C
boiling point	106 ° C
Vapor pressure	25.6 hPa (20 ° C)
solubility	decomposes in water with violent reaction soluble in aromatic and halogenated hydrocarbons
Refractive index	1.447 (20 ° C)
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 302-314-317-334 EUH: 014 P: 260-280-301 + 330 + 331-302 + 352-304 + 341-305 + 351 + 338-309 + 310-342 + 311
Toxicological data	640 mg kg −1 ( LD 50 ,  rat ,  oral )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . Refractive index: Na-D line , 20 ° C

Chlorosulfonyl isocyanate is a chemical compound from the isocyanate group . It was first synthesized in 1952 by Roderich Graf and published in 1956.

Extraction and presentation

Chlorosulfonyl isocyanate can be obtained by reacting cyanogen chloride with sulfur trioxide .

${\displaystyle \mathrm {SO_{3}+ClCN\longrightarrow ClSO_{2}NCO} }$

properties

Chlorosulfonyl isocyanate is a flammable, hardly flammable, highly volatile, colorless liquid that smokes in air and has a pungent odor, which decomposes in water and ethanol with violent to explosive reactions. It decomposes at temperatures above 300 ° C. The compound is the most reactive isocyanate known. The angle between Cl-S and N = C is 94 ° and the NCO group is not linear.

use

Chlorosulfonyl isocyanate is used to make other chemical compounds. It converts amines , alcohols and acids into N -chlorosulfonylureas, -urethanes etc.

Individual evidence

1. ↑ ^{a b c d e f g h i j} Entry on chlorosulfonyl isocyanate in the GESTIS substance database of the IFA , accessed on January 10, 2017(JavaScript required) .
2. ↑ ^{a b c} Entry on N-carbonylsulfamoyl chloride. In: Römpp Online . Georg Thieme Verlag, accessed on November 18, 2016.
3. ↑ Data sheet Chlorosulfonyl isocyanate, Lonza quality, 99.0-100.3% (w / w) (T) from Sigma-Aldrich , accessed on November 18, 2016 ( PDF ).
4. ↑ Data sheet chlorosulfonyl isocyanate (PDF) from Merck , accessed on November 18, 2016.
5. ↑ Jerald K. Rasmussen, Alfred Hassner: Recent developments in the synthetic uses of chlorosulfonyl isocyanate. In: Chemical Reviews. 76, 1976, p. 389, doi : 10.1021 / cr60301a004 .
6. ^ Roderich Graf: About the implementation of cyanogen chloride with sulfur trioxide. In: Chemical Reports. 89, 1956, p. 1071, doi : 10.1002 / cber.19560890437 .
7. ↑ Graf, R. "chlorosulfonyl isocyanates" Organic Syntheses , Collected Volume 5, pages 226ff.
8. ↑ Google Patents: Patent EP0294613A1 - Process and system for the continuous production of chlorosulfonyl isocyanate - Google Patents , accessed on November 18, 2016.
9. ^ Durga Nath Dhar, Preeti Dhar: The Chemistry of Chlorosulfonyl Isocyanate . World Scientific, 2002, ISBN 978-981-238-081-4 , pp. 1 ( limited preview in Google Book search).